This invention relates to novel tetracyanoquinodimethane derivatives which are of value as starting materials for the production of polyesters, polyamides, polyurethanes, etc. or for the manufacture of organic semiconductor devices.
7,7,8,8-Tetracyanoquinodimethane (TCNQ) occurs as yellow crystals melting at 293.5 to 296.degree. C. This compound is ready to accept one electron to form a stable anion radical and its derivatives show very small electrical resistance values. Said compound is converted to phenylenedimalononitrile on reduction with thiophenol, mercaptoacetic acid, hydrogen iodide or the like, and the latter is reconverted to TCNQ on oxidation with N-bromosuccinimide. Chemical condensers are among the commercial applications of TCNQ.
A typical process known for the synthesis of TCNQ comprises condensing malononitrile with 1,4-cyclohexanedione and oxidizing the resulting 1,4-bis(dicyanomethylene)cyclohexane with N-bromosuccinimide or bromine in pyridine.
Since TCNQ is thus electrically conductive despite its being an organic compound, it is rewarding to develop processes for synthesizing said compound via other routes or discover conductive compounds skeletally analogous to TCNQ for the research and development of organic conductive substances and for their commercial implementation.
The object of this invention is to provide novel tetracyanoquinodimethane derivatives which are of value as starting materials for the production of polyesters, polyamides, polyurethanes, etc. or for the manufacture of organic semiconductor devices.
The another object of this invention is to provide a process for production of the above-mentioned tetracyanoquinodimethane derivatives.